89588-28-3

Basic information

• Product Name: 1,3,7-trimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purine-8-carbonitrile
• Synonyms: 1H-purine-8-carbonitrile, 2,3,6,7-tetrahydro-1,3,7-trimethyl-2,6-dioxo-
• CAS NO: 89588-28-3
• Molecular Formula: C₉H₉N₅O₂
• Molecular Weight: 219.2001
• Mol File: 89588-28-3.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 440.6°C at 760 mmHg
• Flash Point: 220.3°C
• Density: 1.49g/cm³
• Vapor Pressure: 5.8E-08mmHg at 25°C
• Refractive Index: 1.705
• CAS DataBase Reference: 1,3,7-trimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purine-8-carbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,7-trimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purine-8-carbonitrile(89588-28-3)
• EPA Substance Registry System: 1,3,7-trimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purine-8-carbonitrile(89588-28-3)

Safety Data

• Hazardous Substances Data: 89588-28-3(Hazardous Substances Data)

Usage

General Description

1,3,7-trimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purine-8-carbonitrile is a chemical compound with the molecular formula C9H10N4O2. It is a purine derivative, which is a type of heterocyclic compound that contains a pyrimidine ring fused to an imidazole ring. 1,3,7-trimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purine-8-carbonitrile is known for its pharmacological properties and is often used as a reagent in organic chemistry experiments. It is a white crystalline powder that is relatively stable under normal conditions. Its chemical structure and properties make it useful in drug development and synthesis, and it has potential applications in pharmaceutical research and development.

Upstream product

• 172302-06-6 1,3,7-trimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purine-8-carboxylic acid amide 
• 58-08-2 3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione 
• 151-50-8 potassium cyanide 
• 773837-37-9 sodium cyanide 
• 5415-41-8 8-iodo-1,3,7-trimethyl-3,7-dihydro-1 H-purine-2,6-dione 
• 10381-82-5 8-bromocaffeine 
• 557-21-1 dicyanozinc 
• 506-68-3 bromocyane 
• 6937-66-2 8,8'-mercuribis-caffeine 
• 6336-13-6 8-acetoxymercuri-caffeine 

Downstream Products

• 109595-94-0 8-(1-hydroxy-2-methylamino-1-phenyl-ethyl)-1,3,7-trimethyl-3,7-dihydro-purine-2,6-dione 
• 130906-69-3 8-(2-bromo-1-hydroxy-1-phenyl-ethyl)-1,3,7-trimethyl-3,7-dihydro-purine-2,6-dione 
• 32086-89-8 8-(1-hydroxyethyl)-1,3,7-trimethyl-3,7-dihydro-1H-purine-2,6-dione 

Relevant articles and documents

Electrochemical C?H Functionalization of (Hetero)Arenes—Optimized by DoE

A novel approach towards the activation of different arenes and purines including caffeine and theophylline is presented. The simple, safe and scalable electrochemical synthesis of 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) aryl ethers was conducted using an easy electrolysis setup with boron-doped diamond (BDD) electrodes. Good yields up to 59 percent were achieved. Triethylamine was used as a base as it forms a highly conductive media with HFIP, making additional supporting electrolytes superfluous. The synthesis was optimized using Design of Experiment (DoE) techniques giving a detailed insight to the significance of the reaction parameters. The mechanism was investigated by cyclic voltammetry (CV). Subsequent transition metal-catalyzed as well as metal-free functionalization led to interesting motifs in excellent yields up to 94 percent.

Synthesis of purinecarbonitriles by Pd(0)-catalysed coupling of halopurines with zinc cyanide

Pd(0)-catalysed coupling of halopurines with zinc cyanide allows the smooth introduction of the cyano group into the purine 2-, 6- and 8-positions. Pronounced ligand effects were observed, and tetrakis(tri-2-furylphosphine)palladium(0) was found to be the

Functionalization Including Fluorination of Caffeine, Guanosine Tetraacetate, and Uridine Triacetate using Electrochemical Oxidation

The title compounds have been subjected to electrochemical oxidation with Et3N-3HF as an electrolyte.Caffeine afforded 8-fluorocaffeine as a sole product in 43percent yield.Guanosine tetraacetate and uridine triacetate gave the fluorinated compounds in 7.3 and 4.8 percent yield, respectively.Similar electrochemical oxidation of caffeine with methanol, KCl or KCN yielded 8-methoxycaffeine, 8-chlorocaffeine, or 8-cyanocaffeine, respecticvely.